Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones

Abstract

SummaryThe cesium carbonate-mediated reaction of 2-bromoallyl sulfones and ortho-hydroxychalcones furnished 3-arylsulfonyl-4H-chromene derivatives in 58–67% yield (18 examples). 2-Bromoallyl sulfones functioned as synthetic surrogates for allenyl sulfones in the reaction.

Advancements in the Preparation of 4H‐Chromenes: An Overview

“…Menon et al . reported a facile synthesis of 4 H ‐chromenes via a base‐mediated annulation of ortho ‐hydroxychalcones 67 and 2‐bromoallyl sulfones 392 [88a] . The reaction proceeded smoothly with regard to both substrates, affording the desired products 393 in 58–67% yields at room temperature for 4 h (Scheme 92).…”

Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones

“…Later, a base mediated operationally simple protocol which gives access to 3-sulfonyl-4 H -chromenes 174 was reported by Thadkapally et al 78 The reaction utilizes o -hydroxychalcones 77 and 2-bromoallyl sulfones 173 as substrates (Scheme 67). Cs 2 CO 3 , which is the base used in this reaction, facilitates the debromination of the 2-bromoallyl sulfone to generate the reactive allenyl sulfone in situ .…”

Ethylenediamine Functionalized Cellulose Acetate [CAEDA] Nanosized Solid Base Catalyst in the Synthesis of 2‐Amino‐4H‐Chromenes and 5‐Substituted‐1H‐Tetrazoles

“…[34,35] Compound (7) shows anti-bacterial activity and compound (8) and (9) acts as anti-cancer alkaloids. [36] Nitrochromene (10) and nitrocoumarin (11) acts as inhibitors of phosphatidylinositol specific phospholipase. [37] DNA dependent protein kinase activity has been inhibited by derivatives of 2-amino-4H-chromene (12) i.e chromen-2-one, chromen-4-one and pyrimidoisoquinolin-4-one.…”

“…One of its derivatives i.e crolibulin (EPC2407) (7‐A) is used to treat solid tumors [34,35] . Compound (7) shows anti‐bacterial activity and compound (8) and (9) acts as anti‐cancer alkaloids [36] . Nitrochromene (10) and nitrocoumarin (11) acts as inhibitors of phosphatidylinositol specific phospholipase [37] .…”